Pentanedioic acid

• Formula: C₅H₈O₄
• Molecular weight: 132.1146
• IUPAC Standard InChI: InChI=1S/C5H8O4/c6-4(7)2-1-3-5(8)9/h1-3H2,(H,6,7)(H,8,9) Copy

  
• IUPAC Standard InChIKey: JFCQEDHGNNZCLN-UHFFFAOYSA-N Copy
• CAS Registry Number: 110-94-1
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
  The 3d structure may be viewed using Java or Javascript.
• Other names: Glutaric acid; 1,3-Propanedicarboxylic acid; 1,5-Pentanedioic acid; Pentandioic acid
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • References
  • Notes
• Other data available:
  • Henry's Law data
• Options:
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• NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

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Condensed phase thermochemistry data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Phase change data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled as indicated in comments:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
DH - Eugene S. Domalski and Elizabeth D. Hearing

Reduced pressure boiling point

Enthalpy of vaporization

Antoine Equation Parameters

log₁₀(P) = A − (B / (T + C))
    P = vapor pressure (bar)
    T = temperature (K)

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Enthalpy of sublimation

Enthalpy of fusion

Enthalpy of phase transition

Entropy of phase transition

Reaction thermochemistry data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: John E. Bartmess

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.

Individual Reactions

C₅H₇O₄^- +  =

By formula: C₅H₇O₄^- + H⁺ = C₅H₈O₄

Gas phase ion energetics data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: John E. Bartmess

De-protonation reactions

C₅H₇O₄^- +  =

By formula: C₅H₇O₄^- + H⁺ = C₅H₈O₄

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

• SOLID (NUJOL MULL); DOW KBr FOREPRISM-GRATING; DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm^-1 resolution

Data compiled by: Timothy J. Johnson, Tanya L. Myers, Yin-Fong Su, Russell G. Tonkyn, Molly Rose K. Kelly-Gorham, and Tyler O. Danby

• solid; Bruker Tensor 37 FTIR; 0.96450084 cm^-1 resolution

Mass spectrum (electron ionization)

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Additional Data

References

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

El-Sayed, 1993
El-Sayed, N.I., The enthalpy of combustion and formation of hydantoin, Asian J. Chem., 1993, 5, 199-207. [all data]

Wilhoit and Shiao, 1964
Wilhoit, R.C.; Shiao, D., Thermochemistry of biologically important compounds. Heats of combustion of solid organic acids., J. Chem. Eng. Data, 1964, 9, 595-599. [all data]

Verkade, Hartman, et al., 1926
Verkade, P.E.; Hartman, H.; Coops, J., Calorimetric researches. X. Heats of combustion of successive terms of homologous series: dicarboxylic acids of the oxalic acid series, Rec. Trav. Chim. Pays/Bas, 1926, 45, 373-393. [all data]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]

Verkade, Hartman, et al., 1924
Verkade, P.E.; Hartman, H.; Coops, J., Jr., Chemistry - The molecular heat of combustion of successive terms of homologous series, Kom. Med. Akad. Ueknschap. Proc., 1924, 27, 859-866. [all data]

Roux, Temprado, et al., 2005
Roux, Maria Victoria; Temprado, Manuel; Chickos, James S., Vaporization, fusion and sublimation enthalpies of the dicarboxylic acids from C4 to C14 and C16, The Journal of Chemical Thermodynamics, 2005, 37, 9, 941-953, https://doi.org/10.1016/j.jct.2004.12.011 . [all data]

Ribeiro da Silva, Monte, et al., 1999
Ribeiro da Silva, Manuel A.V.; Monte, Manuel J.S.; Ribeiro, José R., Vapour pressures and the enthalpies and entropies of sublimation of five dicarboxylic acids, The Journal of Chemical Thermodynamics, 1999, 31, 8, 1093-1107, https://doi.org/10.1006/jcht.1999.0522 . [all data]

Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc., Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]

Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw, Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2 . [all data]

Stull, 1947
Stull, Daniel R., Vapor Pressure of Pure Substances. Organic and Inorganic Compounds, Ind. Eng. Chem., 1947, 39, 4, 517-540, https://doi.org/10.1021/ie50448a022 . [all data]

Cappa, Lovejoy, et al., 2007
Cappa, Christopher D.; Lovejoy, Edward R.; Ravishankara, A.R., Determination of Evaporation Rates and Vapor Pressures of Very Low Volatility Compounds: A Study of the C ₄ -C ₁₀ and C ₁₂ Dicarboxylic Acids, J. Phys. Chem. A, 2007, 111, 16, 3099-3109, https://doi.org/10.1021/jp068686q . [all data]

Chattopadhyay and Ziemann, 2005
Chattopadhyay, Sulekha; Ziemann, Paul J., Vapor Pressures of Substituted and Unsubstituted Monocarboxylic and Dicarboxylic Acids Measured Using an Improved Thermal Desorption Particle Beam Mass Spectrometry Method, Aerosol Science and Technology, 2005, 39, 11, 1085-1100, https://doi.org/10.1080/02786820500421547 . [all data]

Good and Rodriguez-Hornedo, 2009
Good, David J.; Rodriguez-Hornedo, Nair, Solubility Advantage of Pharmaceutical Cocrystals, Crystal Growth & Design, 2009, 9, 5, 2252-2264, https://doi.org/10.1021/cg801039j . [all data]

Ha, Hamilton, et al., 2009
Ha, Jeong-Myeong; Hamilton, Benjamin D.; Hillmyer, Marc A.; Ward, Michael D., Phase Behavior and Polymorphism of Organic Crystals Confined within Nanoscale Chambers, Crystal Growth & Design, 2009, 9, 11, 4766-4777, https://doi.org/10.1021/cg9006185 . [all data]

Steele, Chirico, et al., 2002
Steele, W.V.; Chirico, R.D.; Cowell, A.B.; Knipmeyer, S.E.; Nguyen, A., Thermodynamic Properties and Ideal-Gas Enthalpies of Formation for 1,4-Diisopropylbenzene, 1,2,4,5-Tetraisopropylbenzene, Cyclohexanone Oxime, Dimethyl Malonate, Glutaric Acid, and Pimelic Acid, J. Chem. Eng. Data, 2002, 47, 4, 725-739, https://doi.org/10.1021/je010088b . [all data]

Acree, 1991
Acree, William E., Thermodynamic properties of organic compounds: enthalpy of fusion and melting point temperature compilation, Thermochimica Acta, 1991, 189, 1, 37-56, https://doi.org/10.1016/0040-6031(91)87098-H . [all data]

Petropavlov, Tsygankova, et al., 1988
Petropavlov, N.N.; Tsygankova, I.G.; Teslenko, L.A., Microcalorimetric investigation of polymorphic transitions in organic crystals, Sov. Phys. Crystallogr., 1988, 33(6), 853-855. [all data]

Cingolani and Berchiesi, 1974
Cingolani, A.; Berchiesi, G., Thermodynamic properties of organic compounds. 1. A DSC study of phase transitions in aliphatic dicarboxylic acids, J. Therm. Anal., 1974, 6, 87-90. [all data]

Kumar, Prabhakar, et al., 2005
Kumar, M.R.; Prabhakar, S.; Nagaveni, V.; Vairamani, M., Estimation of gas-phase acidities of a series of dicarboxylic acids by the kinetic method, Rapid Commun. Mass Spectrom., 2005, 19, 8, 1053-1057, https://doi.org/10.1002/rcm.1888 . [all data]

Notes

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), References

• Symbols used in this document:
  

  Tboil	Boiling point
  Tfus	Fusion (melting) point
  ΔHtrs	Enthalpy of phase transition
  ΔStrs	Entropy of phase transition
  ΔcH°solid	Enthalpy of combustion of solid at standard conditions
  ΔfH°solid	Enthalpy of formation of solid at standard conditions
  ΔfusH	Enthalpy of fusion
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔsubH	Enthalpy of sublimation
  ΔsubH°	Enthalpy of sublimation at standard conditions
  ΔvapH	Enthalpy of vaporization
  ΔvapH°	Enthalpy of vaporization at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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